Acetone → 3-(8,9-Dihydroxynonyl)-1-methylthymine
Reaction equation
[CH3:1][N:2]1[CH:10]=[C:8]([CH3:9])[C:6](=[O:7])[N:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC=C)[C:3]1=[O:4].C[N+]1([O-])CC[O:24]CC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:36][C:37]([CH3:39])=[O:38]>O>[OH:38][CH:37]([CH2:39][OH:24])[CH2:36][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:5]1[C:6](=[O:7])[C:8]([CH3:9])=[CH:10][N:2]([CH3:1])[C:3]1=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-methyl-3-(8-nonenyl)thymine (2.63 g, 9.9 mmol), 4-methylmorpholine-N oxide (1.39 g, 12 mmol), and potassium osmate (IV) dihydrate (7 mg, 2×10-5 mol) in acetone (20 mL) and water (10 mL) was stirred for 18 hours. After addition of a saturated aqueous solution of sodium hydrosulfite (10 mL) and 15 minutes of stirring, the reaction mixture was extracted with dichloromethane (50 mL) and with dichloromethane/20% methanol (2×50 mL). The combined organic layers were washed with water (15 mL) and saturated aqueous salt solution (15 mL), and then dried over sodium sulfate. The solvent was evaporated under vacuum to give a white solid residue. The solid was recrystallized in ethanol to yield 2.68 g (91% yield) 3-(8,9-dihydroxynonyl)-1-methylthymine (inventive compound no. 1918).
Workup
- extractionthe reaction mixture was extracted with dichloromethane (50 mL) and with dichloromethane/20% methanol (2×50 mL)
- washThe combined organic layers were washed with water (15 mL) and saturated aqueous salt solution (15 mL)
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under vacuum
- customto give a white solid residue
- customThe solid was recrystallized in ethanol
Sources & evidence
- ORD record
- ord-140252aafb774023898fc04b66b2ff31
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05866576
Reaction notes
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